During the 1999–2000 English football season, Stockport County F.C.

In the 1999–2000 season, Andy Kilner replaced Gary Megson as Stockport's manager in the summer.

Stockport had a brilliant first half of the campaign and on Boxing Day, they sat in the play-off places but afterwards came a dramatic slide in form with just 2 wins from the next 22 league games and Stockport finished the season in a disappointing 17th place.

Note: Flags indicate national team as defined under FIFA eligibility rules; some limited exceptions apply.

Note: Flags indicate national team as defined under FIFA eligibility rules; some limited exceptions apply.